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Structure Database (LMSD)

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Common Name

7alpha-Hydroxydehydroepiandrosterone

Systematic Name

3β,7α-dihydroxy-androst-5-en-17-one

Synonyms

LM ID

LMST02020101

Formula

C₁₉H₂₈O₃

Exact Mass

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304.203846

Sum Composition

ST 19:2;O3

Status

Curated

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Classification

Biological Context

7α-hydroxy Dehydroepiandrosterone (7α-hydroxy DHEA) is an active metabolite of the endogenous steroid hormone dehydroepiandrosterone .¹ 7α-hydroxy DHEA is formed from dehydroepiandrosterone via 7-hydroxylation by cytochrome P450s (CYPs).² It increases antigen-induced production of anti-tetanus toxoid and anti-pertussis antigen IgGs in co-cultures of human tonsil-derived B and T cells when used at a concentration of 1 µM.³ 7α-hydroxy DHEA (6.25 mg/kg) increases serum concentrations of anti-lysozyme IgG in mice.¹

This information has been provided by Cayman Chemical

References

1. Lafaye, P., Chmielewski, V., Nato, F., et al. The 7α-hydroxysteroids produced in human tonsils enhance the immune response to tetanus toxoid and Bordetella pertussis antigens. Biochim. Biophys. Acta 1472(1-2), 222-231 (1999).

2. Hampl, R., Morfin, R., and Starka, L. 7-Hydroxylated derivatives of dehydroepiandrosterone: What are they good for? Endocr. Regul. 31(4), 211-218 (1997).

3. Morfin, R., and Courchay, G. Pregnenolone and dehydroepiandrosterone as precursors of native 7-hydroxylated metabolites which increase the immune response in mice. J. Steroid Biochem. Mol. Biol. 50(1-2), 91-100 (1994).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

The 7alpha-hydroxysteroids produced in human tonsils enhance the immune response to tetanus toxoid and Bordetella pertussis antigens.,
Biochim Biophys Acta, 1999

Pubmed ID: 10572944

String Representations

InChiKey (Click to copy)

OLPSAOWBSPXZEA-JIEICEMKSA-N

InChi (Click to copy)

InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)10-15(21)17-13-3-4-16(22)19(13,2)8-6-14(17)18/h10,12-15,17,20-21H,3-9H2,1-2H3/t12-,13-,14-,15+,17-,18-,19-/m0/s1

SMILES (Click to copy)

[C@@]12([H])[C@H](O)C=C3C[C@@H](O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)C(=O)CC[C@@]21[H]